Oxygenated verticillene derivatives from Bursera suntui.
Medium polarity fractions of the hexane extracts of the stems of Bursera suntui afforded six previously known (1-6) and four hitherto unknown verticillane derivatives: (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol (7), (1S,3Z,7S,8S,11S,12S)-(+)-7,8-epoxyverticill-3-en-12,20-diol 20-acetate (8), (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol (9), and (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 20-acetate (10). Acetylation of 9 and 10 yielded (1S,3Z,7S,11S,12S)-(+)-verticilla-3,8(19)-dien-7,12,20-triol 7,20-diacetate (11), while hydrolysis of 8 gave 7. The structures and stereochemistry of 7-11 were established by spectroscopic analyses, particularly by 1D and 2D NMR spectra and HRESIMS. The conformational preferences of 7-11 were studied by molecular mechanics modelling employing the Monte Carlo protocol followed by B3LYP/DGDZVP DFT calculation, thus supporting the observed (1)H NMR NOESY cross peaks.
García-Gutiérrez
Hugo A
HA
Departamento de Química y Programa de Posgrado en Farmacología, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, Mexico city 07000, Mexico.
Cerda-García-Rojas
Carlos M
CM
Hernández-Hernández
Juan D
JD
Román-Marín
Luisa U
LU
Joseph-Nathan
Pedro
P
D031233:Bursera / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry
D004224:Diterpenes; D010936:Plant Extracts; D010100:Oxygen